GB1455728A - 5-6-benzene ring substituted benzimidazole-2-carbamate deriva tives having anthelmintic activity - Google Patents
5-6-benzene ring substituted benzimidazole-2-carbamate deriva tives having anthelmintic activityInfo
- Publication number
- GB1455728A GB1455728A GB5792573A GB5792573A GB1455728A GB 1455728 A GB1455728 A GB 1455728A GB 5792573 A GB5792573 A GB 5792573A GB 5792573 A GB5792573 A GB 5792573A GB 1455728 A GB1455728 A GB 1455728A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon atoms
- carbamate
- benzene ring
- ring substituted
- substituted benzimidazole
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- WEYSQARHSRZNTC-UHFFFAOYSA-N 1h-benzimidazol-2-ylcarbamic acid Chemical class C1=CC=C2NC(NC(=O)O)=NC2=C1 WEYSQARHSRZNTC-UHFFFAOYSA-N 0.000 title abstract 2
- 230000000507 anthelmentic effect Effects 0.000 title abstract 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 5
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003342 alkenyl group Chemical group 0.000 abstract 2
- 125000000304 alkynyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000004480 active ingredient Substances 0.000 abstract 1
- 230000000843 anti-fungal effect Effects 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- BWHLPLXXIDYSNW-UHFFFAOYSA-N ketorolac tromethamine Chemical compound OCC(N)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1 BWHLPLXXIDYSNW-UHFFFAOYSA-N 0.000 abstract 1
- 239000008194 pharmaceutical composition Substances 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 238000006467 substitution reaction Methods 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C335/00—Thioureas, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
- C07C335/30—Isothioureas
- C07C335/38—Isothioureas containing any of the groups, X being a hetero atom, Y being any atom
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P33/00—Antiparasitic agents
- A61P33/10—Anthelmintics
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
- C07D235/24—Benzimidazoles; Hydrogenated benzimidazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D235/30—Nitrogen atoms not forming part of a nitro radical
- C07D235/32—Benzimidazole-2-carbamic acids, unsubstituted or substituted; Esters thereof; Thio-analogues thereof
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Veterinary Medicine (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Medicinal Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Pharmacology & Pharmacy (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Tropical Medicine & Parasitology (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US31929972A | 1972-12-29 | 1972-12-29 | |
US417963A US3929821A (en) | 1972-12-29 | 1973-11-21 | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1455728A true GB1455728A (en) | 1976-11-17 |
Family
ID=26981949
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB5792573A Expired GB1455728A (en) | 1972-12-29 | 1973-12-13 | 5-6-benzene ring substituted benzimidazole-2-carbamate deriva tives having anthelmintic activity |
GB3023476A Expired GB1456497A (en) | 1972-12-29 | 1973-12-13 | 5-6-benzene ring substituted benzimidazole-2-carbamate derivatives |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3023476A Expired GB1456497A (en) | 1972-12-29 | 1973-12-13 | 5-6-benzene ring substituted benzimidazole-2-carbamate derivatives |
Country Status (25)
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2843008A1 (de) * | 1977-10-06 | 1979-04-19 | Montedison Spa | 5(6)-eckige klammer auf (cyclopropylethyl)-sulphinyl eckige klammer zu -benzimidazol-2-methylcarbamat, ein verfahren zu seiner herstellung, sowie pharmazeutische zusammensetzung |
US4299837A (en) | 1979-12-05 | 1981-11-10 | Montedison S.P.A. | Anthelmintic benzimidazole-carbamates |
Families Citing this family (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4002640A (en) * | 1972-12-29 | 1977-01-11 | Syntex (U.S.A.) Inc. | 5(6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
US4258198A (en) * | 1973-05-29 | 1981-03-24 | Smithkline Corporation | 5-Cycloalkyl thio- and oxy-2-carbalkoxyaminobenzimidazoles |
DE2441201C2 (de) * | 1974-08-28 | 1986-08-07 | Hoechst Ag, 6230 Frankfurt | Anthelminthisch wirksame 2-Carbalkoxyamino-5(6)-phenyl-sulfonyloxy-benzimidazole und Verfahren zu ihrer Herstellung |
DE2441202C2 (de) * | 1974-08-28 | 1986-05-28 | Hoechst Ag, 6230 Frankfurt | 2-Carbalkoxyamino-benzimidazolyl-5(6)-sulfonsäure-phenylester, Verfahren zu ihrer Herstellung und diese enthaltende anthelmintische Mittel |
US4086235A (en) * | 1976-04-12 | 1978-04-25 | Syntex (U.S.A.) Inc. | 5 (6)-Benzene ring substituted benzimidazole-2-carbamate derivatives having anthelmintic activity |
USRE30990E (en) * | 1976-07-16 | 1982-07-06 | E. R. Squibb & Sons, Inc. | Benzimidazole derivatives, compositions thereof and method of use as anthelmintics |
US4046908A (en) * | 1976-07-16 | 1977-09-06 | E. R. Squibb & Sons, Inc. | Benzimidazole derivatives, compositions thereof and method of use as anthelmintics |
US4166858A (en) * | 1976-08-13 | 1979-09-04 | Burroughs Wellcome Co. | Method and composition for treating fluke infections |
FR2361109A1 (fr) * | 1976-08-13 | 1978-03-10 | Wellcome Found | Medicaments anthelminthiques |
FR2362116A1 (fr) * | 1976-08-20 | 1978-03-17 | Oreal | Metaphenylenediamines et compositions tinctoriales les contenant |
US4093732A (en) * | 1977-02-17 | 1978-06-06 | E. R. Squibb & Sons, Inc. | Sulfoxide derivatives of benzimidazoles |
IT1076022B (it) * | 1977-04-20 | 1985-04-22 | Montedison Spa | Benzimidazolcarbammati antielmintici |
US4152522A (en) * | 1978-01-03 | 1979-05-01 | Ethyl Corporation | Process for the preparation of 2-benzimidazole carbamates |
US4136174A (en) * | 1978-01-18 | 1979-01-23 | E. R. Squibb & Sons, Inc. | Benzimidazolecarbamates and method |
US4156006A (en) * | 1978-01-09 | 1979-05-22 | E. R. Squibb & Sons, Inc. | Vinyl sulfide derivatives of benzimidazoles |
JPS54104837A (en) * | 1978-02-03 | 1979-08-17 | Nippon Denso Co Ltd | Controller of copying machines |
US4145431A (en) * | 1978-02-16 | 1979-03-20 | E. R. Squibb & Sons, Inc. | Method of treating helminthiasis by parenteral administration of sulfide- and sulfoxide-derivatives of benzimidazoles |
US4154846A (en) * | 1978-06-16 | 1979-05-15 | E. R. Squibb & Sons, Inc. | Substituted thio-, sulfinyl-, and sulfonyl-alkyl benzimidazole carbamates |
US4174400A (en) * | 1978-09-13 | 1979-11-13 | Merck & Co., Inc. | Anthelmintic benzimidazoles |
DE2845537A1 (de) * | 1978-10-19 | 1980-04-30 | Bayer Ag | Benzimidazolylcarbamidsaeureester, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
IT1100788B (it) * | 1978-12-06 | 1985-09-28 | Montedison Spa | Benzimidazol-carbammati |
SE445641B (sv) * | 1978-12-06 | 1986-07-07 | Montedison Spa | Bensimidazolkarbamat och forfarande for framstellning derav |
US4198422A (en) * | 1979-05-17 | 1980-04-15 | E. R. Squibb & Sons, Inc. | Substituted 2,3-naphthimidazole carbamates and method |
EP0028455A1 (en) * | 1979-10-12 | 1981-05-13 | Imperial Chemical Industries Plc | 5-Phenylselenobenzimidazole derivatives, their preparation and anthelmintic or fasciolicidal compositions containing them |
US4599428A (en) * | 1979-10-19 | 1986-07-08 | Chinoin Gyogyszer Es Vegyeszeti Termekek Gyara Rt | Process for the preparation of 5(6)-thio substituted benzimidazoles |
HU182763B (hu) * | 1979-10-19 | 1984-03-28 | Chinoin Gyogyszer Es Vegyeszet | Eljárás 5(6)-alkiltio-benzimidazolil-alkil-karbamátok előállítására |
IL61232A (en) * | 1979-10-19 | 1985-09-29 | Chinoin Gyogyszer Es Vegyeszet | Process for the preparation of 2-amino(or alkoxycarbonylamino)-5(6)-thiocyanato(or thiol)benzimidazole derivatives |
DE3719783A1 (de) * | 1987-06-13 | 1988-12-22 | Hoechst Ag | Verfahren zur herstellung von 5-phenylsulfinyl-1h-2-(methoxycarbonylamino)- benzimidazol |
GB9205368D0 (en) * | 1992-03-12 | 1992-04-22 | Pfizer Ltd | Benzimidozole anthelmintic agents |
US6593466B1 (en) | 1999-07-07 | 2003-07-15 | Isis Pharmaceuticals, Inc. | Guanidinium functionalized nucleotides and precursors thereof |
CA2616512A1 (en) * | 2005-07-28 | 2007-02-08 | Intervet International B.V. | Novel benzimidazole (thio) carbamates with antiparasitic activity and the synthesis thereof |
US20130197527A1 (en) * | 2006-06-12 | 2013-08-01 | Smith & Nephew, Inc. | Systems, methods and devices for tibial resection |
AR061351A1 (es) | 2006-06-14 | 2008-08-20 | Intervet Int Bv | Composicion de carbamato de bencimidazol |
CN102241635A (zh) * | 2011-04-28 | 2011-11-16 | 江苏宝众宝达药业有限公司 | 一种苯并咪唑类驱虫药苯硫咪唑的制备方法 |
CN102863392A (zh) * | 2012-10-18 | 2013-01-09 | 江苏宝众宝达药业有限公司 | 一种奥芬达唑生产过程中大幅减少溶剂使用量的方法 |
Family Cites Families (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2933502A (en) * | 1958-02-12 | 1960-04-19 | Du Pont | Benzimidazolone derivatives |
US2933504A (en) * | 1959-08-10 | 1960-04-19 | Du Pont | Derivatives of polyalkoxycarbonyl imine |
US3010968A (en) | 1959-11-25 | 1961-11-28 | Du Pont | Process for manufacture of certain alkyl esters of benzimidazole carbamic acids |
BE666795A (enrdf_load_stackoverflow) * | 1964-08-04 | 1966-01-13 | ||
US3506767A (en) * | 1965-08-06 | 1970-04-14 | Geigy Chem Corp | Benzimidazole compositions and methods of use |
US3401171A (en) * | 1966-03-11 | 1968-09-10 | Smithkline Corp | 2-amidobenzimidazoles |
CH456236A (de) * | 1966-05-06 | 1968-07-15 | Agripat Sa | Verfahren zum Schützen textiler Keratinfasermaterialien vor Insektenfrass und Mittel zur Durchführung dieses Verfahrens |
US3480642A (en) * | 1967-03-22 | 1969-11-25 | Smithkline Corp | Process for producing 2-carbalkoxyaminobenzimidazoles |
CH490010A (de) * | 1967-10-26 | 1970-05-15 | Ciba Geigy | Schädlingsbekämpfungsmittel |
US3562290A (en) * | 1967-11-07 | 1971-02-09 | Du Pont | Process for making 2-benzimidazolecarbamic acid alkyl esters |
FR2059938A1 (en) * | 1969-03-14 | 1971-06-11 | Aries Robert | 1-haloalk(en)yl sulphenyl-2-aryloxycarbon-yl - |
US3657267A (en) * | 1969-06-20 | 1972-04-18 | Janssen Pharmaceutica Nv | Benzimidazole carbamates |
US3714180A (en) * | 1970-08-12 | 1973-01-30 | Squibb & Sons Inc | Sulfonyl benzimidazoles |
US3694455A (en) * | 1970-11-19 | 1972-09-26 | Smith Kline French Lab | Acyloxyalkyl amidobenzimidazoles |
US3720686A (en) * | 1971-04-01 | 1973-03-13 | Squibb & Sons Inc | Mercaptobenzimidazole derivatives |
-
1973
- 1973-11-21 US US417963A patent/US3929821A/en not_active Expired - Lifetime
- 1973-12-10 IN IN2692/CAL/73A patent/IN138644B/en unknown
- 1973-12-13 GB GB5792573A patent/GB1455728A/en not_active Expired
- 1973-12-13 GB GB3023476A patent/GB1456497A/en not_active Expired
- 1973-12-14 CH CH1760073A patent/CH613955A5/xx not_active IP Right Cessation
- 1973-12-14 CH CH68577A patent/CH608006A5/xx not_active IP Right Cessation
- 1973-12-17 DK DK685273AA patent/DK137329B/da not_active IP Right Cessation
- 1973-12-19 IL IL43860A patent/IL43860A/en unknown
- 1973-12-20 DE DE2363351A patent/DE2363351C2/de not_active Expired
- 1973-12-20 DE DE19732366069 patent/DE2366069A1/de active Granted
- 1973-12-20 SE SE7317261A patent/SE414402B/sv unknown
- 1973-12-20 HU HUSI1367A patent/HU169272B/hu unknown
- 1973-12-20 DE DE2366070A patent/DE2366070C2/de not_active Expired
- 1973-12-21 IE IE2322/73A patent/IE40046B1/xx unknown
- 1973-12-21 CS CS738891A patent/CS187390B2/cs unknown
- 1973-12-21 RO RO7377156A patent/RO67150A/ro unknown
- 1973-12-21 AT AT1075173A patent/AT332883B/de active
- 1973-12-26 JP JP744829A patent/JPS5939428B2/ja not_active Expired
- 1973-12-27 YU YU3371/73A patent/YU36706B/xx unknown
- 1973-12-28 AR AR251776A patent/AR216037A1/es active
- 1973-12-28 BR BR10296/73A patent/BR7310296D0/pt unknown
- 1973-12-28 FR FR7346946A patent/FR2212150B1/fr not_active Expired
- 1973-12-28 NL NLAANVRAGE7317797,A patent/NL169738C/xx not_active IP Right Cessation
- 1973-12-28 SU SU731980901A patent/SU727143A3/ru active
- 1973-12-28 IT IT7901/73A patent/IT1046097B/it active Protection Beyond IP Right Term
- 1973-12-29 ES ES421927A patent/ES421927A1/es not_active Expired
- 1973-12-29 PL PL1973167768A patent/PL95987B1/pl unknown
-
1976
- 1976-02-17 ES ES445257A patent/ES445257A1/es not_active Expired
- 1976-05-06 AR AR263212A patent/AR221816A1/es active
-
1980
- 1980-03-06 HK HK82/80A patent/HK8280A/xx unknown
- 1980-03-07 YU YU641/80A patent/YU40868B/xx unknown
- 1980-12-30 MY MY273/80A patent/MY8000273A/xx unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2843008A1 (de) * | 1977-10-06 | 1979-04-19 | Montedison Spa | 5(6)-eckige klammer auf (cyclopropylethyl)-sulphinyl eckige klammer zu -benzimidazol-2-methylcarbamat, ein verfahren zu seiner herstellung, sowie pharmazeutische zusammensetzung |
US4299837A (en) | 1979-12-05 | 1981-11-10 | Montedison S.P.A. | Anthelmintic benzimidazole-carbamates |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
746B | Proceeding under section 46(3) patents act 1977 | ||
746B | Proceeding under section 46(3) patents act 1977 | ||
CTFF | Supplementary protection certificate filed |
Free format text: SPC/GB93/105, 930628 |
|
CTFG | Supplementary protection certificate granted |
Free format text: SPC/GB93/105, 931126, EXPIRES:19981212 |
|
PE20 | Patent expired after termination of 20 years |
Effective date: 19931212 |
|
CTFE | Supplementary protection certificate entered into force |
Free format text: SPC/GB93/105, 931213, EXPIRES:19981212 |
|
CTFG | Supplementary protection certificate granted |
Free format text: SPC/GB93/105, 931213, EXPIRES:19981212 |
|
CTFG | Supplementary protection certificate granted |
Free format text: SPC/GB93/105, 931126 ERRATUM IN OJ(P)5465 PAGE 5739, EXPIRES:YYYYMMDD |
|
SPCE | Supplementary protection certificate expired |
Free format text: SPC/GB93/105, 981212 |
|
SPCE | Supplementary protection certificate expired |
Free format text: SPC/GB93/105, 981212 |